Dear Dr. Date,It’…

Dear Dr. Date,
It’s like this, you see … I’m a really nice guy — interesting, quirky, funny and sensitive. I care a lot about my friends and about the women that I’ve dated. I care not because of who I think they are, but for who they are as people and for the love they show toward me. Somehow it ends up with tragically funny lines like “I love you too much to go out with you” or “You’re so much a brother to me that I don’t want to hurt you.”
In hindsight, I realize that some of these relationships were bound to fail (a unitarian with someone who revealed herself to be a right-wing Christian for example) … and I laugh about the whole bit. So how do I show interest without being overboard? I’m a moderately sensitive guy so I don’t want to overextend myself. What is your advice, good doctor?
— Supposedformerlovefool
My friend, you’re going to have to push your limits. Generally speaking — something I generally hate to do — people that are worried about being too bold are so far away from actually being bold that they can only be called timid. I know exactly what you are afraid of being. You don’t want to appear super slick, untrustworthy and slimy when you approach women with insipid pickup lines. Just don’t use dumb lines. Say what is on your mind and say it proudly and boldly. Of course, I’m assuming that you have fairly appropriate things on your mind.
Nice guys tend to talk too much and share too much. These are both wonderful qualities in a man, but if you do it too soon you can take all the mystery out of yourself and the potential relationship. If you are the type of person that likes to have deep, emotional conversations that expose all sorts of fragile insecurities in a person, then you will undoubtedly end up being only a friend. Again, these conversations are the essence of a healthy, strong relationship, but not a great first date or encounter. Women are human, too, and as such they have the same sort of insecurities and foibles that men do. Think of your worst secret or worst quality. Do you want potential dates to know these things right away? Most likely not. Don’t dig too deeply in the beginning. Concentrate on having fun instead.
Lastly, be more objective. When you are out on the town or at a party and supposedly “slimy” men are picking up all the women, watch them and learn. Some men are slimebags, but most aren’t much different than you. They are interesting, quirky, funny and sensitive — just like you. The only difference is that they are bolder.